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Visible-light photocatalyzed synthesis of 2-aryl N-methylpyrroles, furans and thiophenes utilizing arylsulfonyl chlorides as a coupling partner
Tetrahedron ( IF 2.1 ) Pub Date : 2016-04-15 11:41:10
Palani Natarajan, Anu Bala, S.K. Mehta, K.K. Bhasin

Visible-light (Blue LED lamp: hν=425±15 nm) photocatalyzed cross-coupling reactions of arylsulfonyl chloride with N-methylpyrrole, furan, thiophene and their derivatives have been achieved in moderate to good yields at room temperature. A plausible mechanism has been proposed for the reaction. The arylation takes place at the C–H bond (C2–H or C5–H) next to the heteroatom with a high regioselective manner! Moreover, arylsulfonyl chlorides utilized in this study are inexpensive, environmentally benign and relatively more stable towards temperature, moisture and air as compared to diazonium salts normally used as coupling partners in the previously reported methods for the synthesis of heterobiaryls through visible-light photocatalyzed conditions.

中文翻译:

利用芳基磺酰氯作为偶联伙伴的可见光光催化合成2-芳基N-甲基吡咯,呋喃和噻吩

可见光(蓝色LED灯:hν= 425±15 nm)在室温下以中等至良好的产率实现了芳基磺酰氯与N-甲基吡咯,呋喃,噻吩及其衍生物的光催化交叉偶联反应。已经提出了对该反应的合理机制。芳基化反应在杂原子旁的C–H键(C 2 –H或C 5 –H)上以高区域选择性的方式发生!此外,与先前报道的通过可见光光催化条件合成杂联芳基的方法中通常用作偶合伴侣的重氮盐相比,本研究中使用的芳基磺酰氯价格便宜,对环境无害,并且对温度,湿度和空气相对更稳定。
更新日期:2016-04-16
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